Compound and organic light-emitting device including the same

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer comprises a compound represented by Formula 1. An organic light-emitting device including the compound may have high efficiency, low voltage, high luminance, and a long lifespan.

What is claimed is: 
     
       1. A compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         A 1  to A 8  are each independently selected from CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 , CR 17 , CR 18 , and N, wherein at least one selected from A 1  to A 8  is N; 
         R 1  is selected from deuterium, a halogen group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 60  alkyl group, a substituted or unsubstituted C 2 -C 60  alkenyl group, a substituted or unsubstituted C 2 -C 60  alkynyl group, a substituted or unsubstituted C 1 -C 60  alkoxy group, a substituted or unsubstituted C 3 -C 10  cycloalkyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60  aryl group, a substituted or unsubstituted C 6 -C 60  aryloxy group, a substituted or unsubstituted C 6 -C 60  arylthio group, a substituted or unsubstituted C 1 -C 60  heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, P(═O)R 31 R 32 , P(═S)R 33 R 34 , S(═O) 2 R 35 , and S(═O)R 36 ; 
         R 2  is selected from hydrogen, deuterium, a halogen group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 60  alkyl group, a substituted or unsubstituted C 2 -C 60  alkenyl group, a substituted or unsubstituted C 2 -C 60  alkynyl group, a substituted or unsubstituted C 1 -C 60  alkoxy group, a substituted or unsubstituted C 3 -C 10  cycloalkyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60  aryl group, a substituted or unsubstituted C 6 -C 60  aryloxy group, a substituted or unsubstituted C 6 -C 60  arylthio group, a substituted or unsubstituted C 1 -C 60  heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, P(═O)R 31 R 32 , P(═S)R 33 R 34 , S(═O) 2 R 35 , and S(═O)R 36 ; 
         R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , and R 18  are each independently hydrogen; 
         R 31 , R 32 , R 33 , R 34 , R 35 , and R 36  are each independently selected from hydrogen, deuterium, a halogen group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 60  alkyl group, a substituted or unsubstituted C 6 -C 60  aryl group, a substituted or unsubstituted C 1 -C 60  heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group; 
         L 1  and L 2  are each independently selected from a substituted or unsubstituted C 6 -C 60  arylene group, a substituted or unsubstituted C 1 -C 60  heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group; 
         a1 and a2 are each independently an integer from 0 to 3; 
         m and n are each independently an integer selected from 1 to 2; and 
         at least one substituent of the substituted C 1 -C 60  alkyl group, substituted C 2 -C 60  alkenyl group, substituted C 2 -C 60  alkynyl group, substituted C 1 -C 60  alkoxy group, substituted C 3 -C 10  cycloalkyl group, substituted C 2 -C 10  heterocycloalkyl group, substituted C 3 -C 10  cycloalkenyl group, substituted C 2 -C 10  heterocycloalkenyl group, substituted C 6 -C 60  aryl group, substituted C 6 -C 60  aryloxy group, substituted C 6 -C 60  arylthio group, substituted C 1 -C 60  heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C 6 -C 60  arylene group, substituted C 1 -C 60  heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, and a substituted divalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of: 
         deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, and a C 1 -C 60  alkoxy group, 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, and a C 1 -C 60  alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ), 
         a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and 
         a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ), 
         wherein Q 11  to Q 17  and Q 21  to Q 27  are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. 
       
     
     
       2. The compound of  claim 1 , wherein
 R 31 , R 32 , R 33 , R 34 , R 35 , and R 36  in Formula 1 are each independently a substituted or unsubstituted C 6 -C 60  aryl group. 
 
     
     
       3. The compound of  claim 1 , wherein
 L 1  and L 2  in Formula 1 are each independently one of Formulae 2a to 2d: 
 
       
         
           
           
               
               
           
         
         wherein “*” in Formulae 2a to 2d indicates a binding site. 
       
     
     
       4. The compound of  claim 1 , wherein
 R 1  in Formula 1 is selected from deuterium, a cyano group, P(═O)R 31 R 32 , P(═S)R 33 R 34 , and a group represented by one of Formulae 3a to 3k; 
 and R 2  in Formula 1 is selected from hydrogen, deuterium, a cyano group, P(═O)R 31 R 32 , P(═S)R 33 R 34 , and a group represented by one of Formulae 3a to 3k: 
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein in Formulae 3a to 3k, H 1  is selected from CR 41 R 42 , NR 43 , O, and S; 
         R 41  to R 43 , Z 1 , and Z 2  are each independently selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carboxy group, a substituted or unsubstituted C 1  to C 20  alkyl group, a substituted or unsubstituted C 6  to C 20  aryl group, a substituted or unsubstituted C 1  to C 20  heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group; 
         p in Formulae 3a and 3k is an integer selected from 1 to 4, p in Formula 3c is an integer selected from 1 to 3, p in Formula 3d is an integer selected from 1 to 9, p in Formulae 3e and 3g is an integer selected from 1 to 6, p in Formula 3f is an integer selected from 1 to 5, and p in Formulae 3h, 3i, and 3j is an integer selected from 1 to 7, wherein when p is 2 or more, two or more Z 1 (s) are identical to or different from each other; and 
         * indicates a binding site. 
       
     
     
       5. The compound of  claim 1 , wherein
 the compound of Formula 1 is represented by Formula 2: 
 
       
         
           
           
               
               
           
         
       
     
     
       6. The compound of  claim 1 , wherein
 the compound of Formula 1 is represented by Formula 3: 
 
       
         
           
           
               
               
           
         
       
     
     
       7. The compound of  claim 1 , wherein
 the compound of Formula 1 is represented by Formula 4: 
 
       
         
           
           
               
               
           
         
       
     
     
       8. The compound of  claim 1 , wherein
 the compound of Formula 1 is represented by Formula 5: 
 
       
         
           
           
               
               
           
         
       
     
     
       9. A compound represented by one of Compounds 1 to 113 and 124 to 127: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       10. An organic light-emitting device comprising:
 a first electrode; 
 a second electrode facing the first electrode; and 
 an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer, 
 wherein the organic layer comprises the compound of  claim 1 . 
 
     
     
       11. The organic light-emitting device of  claim 10 , wherein
 the first electrode is an anode, 
 the second electrode is a cathode, and 
 the organic layer comprises:
 i) a hole transport region between the first electrode and the emission layer, the hole transport region comprising at least one selected from a hole transport layer, a hole injection layer, and an electron blocking layer, and 
 ii) an electron transport region between the emission layer and the second electrode, the electron transport region comprising an electron transport layer and at least one selected from a hole blocking layer and an electron injection layer. 
 
 
     
     
       12. The organic light-emitting device of  claim 11 , wherein
 the electron transport region comprises the compound represented by Formula 1. 
 
     
     
       13. The organic light-emitting device of  claim 11 , wherein
 the electron transport layer comprises the compound represented by Formula 1. 
 
     
     
       14. The organic light-emitting device of  claim 11 , wherein
 the hole transport region comprises a charge-generating material. 
 
     
     
       15. The organic light-emitting device of  claim 14 , wherein
 the charge-generating material is a p-dopant. 
 
     
     
       16. The organic light-emitting device of  claim 14 , wherein
 the charge-generating material is HT-D1 or F4-TCNQ: 
 
       
         
           
           
               
               
           
         
       
     
     
       17. The organic light-emitting device of  claim 11 , wherein
 the electron transport region comprises a metal-containing material. 
 
     
     
       18. The organic light-emitting device of  claim 11 , wherein
 the electron transport region comprises ET-D1 or ET-D2: 
 
       
         
           
           
               
               
           
         
       
     
     
       19. A display apparatus comprising the organic light-emitting device of  claim 10 , wherein the first electrode of the organic light-emitting device is electrically coupled to a source electrode or a drain electrode of a thin film transistor.